As an update. I was able to get plex up and running again. I noticed after uninstalling plex the folder /var/lib/plexmediaserver was still there. I figured it was probably causing issues for whatever I messed up earlier. I deleted that folder and then moved over everything and PMS shows all of my previous stuff from windows. I am now in the process of reading this thread Extremely Frustrated About Permissions and this thread Linux Tips
I’m not master at linux and I’m still learning something new every day. Permissions are not my strong suit and will probably mess this up. From reading it appears that plex won’t be able to access the HDD because once it’s mounted it will be mounted under my username at /media/username/HDD. I’m in the process of figuring out how to unmount it and have it mount somewhere else once it’s plugged in to do sudo chown -R plex:plex /disk/HDD.
